JP6455893B2 - 不斉転換のための有機金属の触媒作用 - Google Patents
不斉転換のための有機金属の触媒作用 Download PDFInfo
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- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
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Description
本出願は、2013年3月11日に提出された米国仮出願番号第61/775,807号に対して米国特許法第119条(e)項に基づく利益を主張するものであり、当該出願の開示は、全体として参照により本明細書中に組み込まれる。
特異な活性化モードを伴う遷移金属触媒作用および有機触媒作用において、非常に多くの優れた触媒が開発されてきている。しかしながら、かような触媒の利用は、反応の範囲が限られていることや、触媒量が多いといった固有の欠点により妨げられている。これらの制限を改善する試みにおいて、近年、遷移金属触媒作用と有機触媒作用とを組み合わせるという構想が浮上している。共同触媒作用、相乗的触媒作用、および連続した/リレー触媒作用といった方策が確立されている。しかしながら、触媒、基質、中間体および溶媒の間の不和合性が潜在的な欠点となっている。
本明細書は、以下の構造またはそのエナンチオマーを有する配位子を開示する:
本明細書は、キラルなビスホスフィンが有機触媒と共有結合により結合することにより、個々の金属触媒および有機触媒と比較して、転化率および選択性が顕著に改善された配位子および当該配位子から調製される触媒を開示する。ビスホスフィンと錯形成した金属は、一般的な触媒であり、高い回転数で、多くの金属触媒反応を促進することができる。有機触媒は、基質を活性化し、選択性に影響を与える。本明細書中に用いられる「有機金属の触媒作用」の用語は、有機触媒部分と共有結合的に結合した金属触媒部分を有する化合物により、触媒される反応およびその触媒を指す。金属部分に由来する高い活性および有機触媒に由来する高い選択性により、不斉触媒における有用な手法が提供される。
「アルキル」の用語は、直鎖のアルキル基および分岐のアルキル基を含む、飽和の脂肪族基のラジカルをいう。「シクロアルキル」の用語は、炭素原子数が約3〜7である非芳香族の単環式または多環式環系をいう。シクロアルキル基の例としては、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル等が挙げられる。
材料および方法
空気または湿気に敏感な化合物を扱う反応は、乾燥容器中、窒素加圧の下、または窒素で満たされたグローブボックス中で行った。他に記載のない限り、すべての試薬および溶媒は、商業用の供給者から購入し、さらに精製は行わなかった。無水溶媒は、シグマ−アルドリッチから購入し、シリンジによって導入した。生成物の精製は、ACROS社製シリカゲル(0.06−0.20mm)を用いたクロマトグラフィーにより行い、分析薄層クロマトグラフィー(TLC)は、Merck社製シリカゲルプレート(GF254)を用いて行った。[Rh(COD)Cl]2、[Rh(COD)2]BF4および[Rh(COD)2]SbF6は、Heraeusから購入した。HPLC溶媒は、Alfa(n−ヘキサン)およびシグマ−アルドリッチ(2−プロパノール)から購入した。
すべてのN−Hイミンは、文献(Hou, G., et al., J. Am. Chem. Soc. 2009, 131, 9882-9883.)に従って調製した。すべてのスペクトルデータは、文献の値と一致した。
Claims (5)
- 以下の式によって表される化合物からなる群から選択される、配位子:
Phは、それぞれ独立して、フェニル;P−CH 3 フェニル;3,5−ジ−CH 3 フェニル;3,5−ジ−t−ブチルフェニル;3,5−ジ−CF 3 フェニル;2−CH 3 フェニル;C 6 F 5 ;2−ナフチル;および1−ナフチルからなる群から選択される。 - 以下の式によって表される化合物からなる群から選択される、配位子:
Phは、それぞれ独立して、フェニル;P−CH 3 フェニル;3,5−ジ−CH 3 フェニル;3,5−ジ−t−ブチルフェニル;3,5−ジ−CF 3 フェニル;2−CH 3 フェニル;C 6 F 5 ;2−ナフチル;および1−ナフチルからなる群から選択され、
Rは、それぞれ独立して、フェニル;P−CH 3 フェニル;3,5−ジ−CH 3 フェニル;3,5−ジ−t−ブチルフェニル;3,5−ジ−CF 3 フェニル;2−CH 3 フェニル;C 6 F 5 ;2−ナフチル;1−ナフチル;t−ブチル;i−プロピル;シクロヘキシルおよびシクロペンチルからなる群から選択される。 - 請求項1および2に記載の配位子のいずれか一つを含み、以下の構造またはそのエナンチオマーを有する触媒:
Rは、前記配位子ごとに定義されるPhまたはR基であり、
Mは、Rh、Pd、Cu、Ru、Ir、Ag、Au、Zn、Ni、Co、およびFeからなる群から選択される。 - アルケンを水素化するために有効な温度および圧力下で、適当な溶媒中、前記アルケンを、過剰量の水素ガスおよび触媒的に有効な量の請求項3に記載の触媒と混合することを含む、アルケンを対応するアルカンに不斉水素化する方法。
- 前記溶媒は、イソプロパノールを含む、請求項4に記載の方法。
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US201361775807P | 2013-03-11 | 2013-03-11 | |
US61/775,807 | 2013-03-11 | ||
PCT/US2014/023519 WO2014164801A1 (en) | 2013-03-11 | 2014-03-11 | Metallorganocatalysis for asymmetric transformations |
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US (1) | US9744528B2 (ja) |
EP (1) | EP2969202A4 (ja) |
JP (2) | JP6455893B2 (ja) |
KR (1) | KR20150127632A (ja) |
CN (2) | CN107954880A (ja) |
CA (1) | CA2901591A1 (ja) |
WO (1) | WO2014164801A1 (ja) |
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US20180332339A1 (en) * | 2017-05-12 | 2018-11-15 | Enseo, Inc. | Set-Top Box with Enhanced Functionality and System and Method for Use of Same |
US10125159B2 (en) * | 2016-10-11 | 2018-11-13 | King Fahd University Of Petroleum And Minerals | Functionalized magnetic nanoparticle, a catalyst, a method for forming C—C bonds |
CN107722068B (zh) * | 2017-11-09 | 2020-05-22 | 凯特立斯(深圳)科技有限公司 | 三齿氮膦配体与其配合物、及其在酮的不对称催化氢化中的应用 |
CN108409802B (zh) * | 2018-02-08 | 2020-08-25 | 浙江工业大学 | 一种(s)-1-二茂铁乙基二甲胺的制备工艺 |
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JPH0761976B2 (ja) * | 1987-01-21 | 1995-07-05 | 住友化学工業株式会社 | 光学活性アリ−ル酢酸誘導体の製造法 |
US4870208A (en) | 1988-06-03 | 1989-09-26 | Monsanto Company | Asymmetric hydrogenolysis of epoxides |
DE69709883T2 (de) * | 1996-10-07 | 2002-08-29 | Syngenta Participations Ag | Chirale ferrocene |
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JP4987197B2 (ja) * | 2001-06-04 | 2012-07-25 | 第一三共株式会社 | 光学活性トリハロアニリノ誘導体の製造方法および光学活性ホスフィン配位子 |
TW200602293A (en) * | 2004-04-05 | 2006-01-16 | Merck & Co Inc | Process for the preparation of enantiomerically enriched beta amino acid derivatives |
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CA2692222A1 (en) * | 2007-07-03 | 2009-01-08 | Sanofi-Aventis | A process for the palladium-catalyzed coupling of terminal alkynes with aryl tosylates |
BRPI0907343A8 (pt) * | 2008-04-17 | 2017-05-23 | United Phosphorus Ltd | Hidrogenação de iminas |
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EP2969202A1 (en) | 2016-01-20 |
CA2901591A1 (en) | 2014-10-09 |
CN105188926B (zh) | 2018-01-09 |
US20160023198A1 (en) | 2016-01-28 |
CN105188926A (zh) | 2015-12-23 |
WO2014164801A1 (en) | 2014-10-09 |
JP2016518322A (ja) | 2016-06-23 |
JP2019089766A (ja) | 2019-06-13 |
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US9744528B2 (en) | 2017-08-29 |
CN107954880A (zh) | 2018-04-24 |
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